Over the last two years that I’ve been in college, the following exchange has happened on at least five different occasions:

Me, noticing Moneyball on a desk/bookshelf/dirty dorm room floor: “Oh, are you a baseball fan?”

Person reading Moneyball: “What? No. Why would you think that?”

Me: “Uhhh…because you’re reading Moneyball?”

Person reading Moneyball: “Oh, that’s just for a business class.”

Certainly, the book has had an impact far beyond the baseball diamond. The genius of Billy Beane wasn’t that he built a great baseball team, but that he did it through his ingenuity. He couldn’t win the normal way, so he found a new one. He took antiquated thinking and capitalized before everyone could catch up; that’s the lesson business school professors are trying to convey when they assign the book to students.

Scott Hatteberg, who was undervalued but got on base, was featured in Michael Lewis’ Moneyball.

The part that’s typically forgotten, however, is the book’s subtitle: The Art of Winning an Unfair Game. When Michael Lewis published the book in 2003, he made Beane’s strategy exponentially harder. Jeff Passan describes that the book, “set into motion the most significant changes in baseball since Jackie Robinson integrated the game in 1947.” Suddenly, Beane was dealt a losing hand once more. He didn’t have the money, and everyone else had his cheat code. Once again, the game was unfair.


I read Moneyball myself when I was in elementary school, a fact from which there are two takeaways: 1) I was a nerd, and 2) I should transfer to business school immediately. Much more lucrative than journalism.

My dad had a coworker who was obsessed with baseball analytics. I would go visit the office, and we would talk baseball. We surely talked about Moneyball, and if we didn’t mention the book by name, we talked about its lessons. One day, he introduced me to a website called Fangraphs that tracks advanced stats. He gave me his premium log-in so that I could read some of the articles.

The next time I saw him, he asked me what I thought. I told him I liked it fine and that the numbers were interesting, but they were only part of the picture. “You can’t capture personality,” I remember telling him. “You can’t build a team just looking at numbers.”

So, yeah. Weird kid.

As I’ve watched baseball the past several years, I’ve thought a lot about what the “next” Moneyball is. What would Billy Beane—or someone like him—do to win now? Clearly I wasn’t the only one interested. Jonah Keri’s book The Extra 2% chronicled how Andrew Friedman—now with the Dodgers—constructed the Tampa Bay Rays. Last year’s bestseller by Mark Reiter was fittingly dubbed Astroball. The subtitle? The New Way to Win it All.

I thought I found the new Moneyball when Theo Epstein and Jed Hoyer actualized my comments from years before in their construction of the drought-breaking Chicago Cubs. They used stats, sure, but they also emphasized culture. They wanted players who lived their lives according to “The Cubs Way,” which was formalized in a lengthy guidebook distributed to every member of the organization. When they poured money into Jon Lester before the 2015 season, it was in large part due to his leadership. Ditto for Jason Heyward in 2016.

President Theo Epstein (right) and GM Jed Hoyer (left) valued culture in building the Cubs. Their manager Joe Maddon (center) is the perfect example of this strategy.

I’ve come to realize that while that’s a good way to win, (it’s part of what put the Houston Astros over the top as well) it doesn’t get to the heart of the Moneyball strategy. Moneyball isn’t about winning baseball games; it’s about winning unfair games.

In 2001, Billy Beane’s disadvantage was money. Now, the money advantage that richer teams possess doesn’t mean they’re signing huge contracts. Instead, that money is invested in superior data and mind power. In 2003, Billy Beane was in the minority. Now, every team in the big leagues has an analytic focus. The brightest minds are the ones in charge of the biggest franchises: the Red Sox, Cubs, Yankees, and Dodgers.

Each of those teams are built on different tenants. Each executive has reached a different conclusion on what the market has come to undervalue in a ballplayer. The Cubs hoard players like Javy Baez and Ben Zobrist who can play multiple positions. The Yankees emphasize power. For the Dodgers, it’s depth: over the last four years, they have fielded at least 52 different players every season.

While the richest teams can’t agree on what they value, they are consistent with regards to what they don’t: superstars with a high price tag. 2018 was the first season in over a decade in which the aggregate payrolls in the MLB decreased. The Yankees fielded their cheapest team since 2003. The Dodgers cut nearly $60 million in salary between 2017 and 2018.

What happened? In short, the players screwed themselves, and baseball teams are exploiting the union’s gaffe. The MLB works today like this: you play for less than minimum wage in the Minors. Then, you’re underpaid during your first six years in the league. After that, you cash in.

When the Players Union agreed to the terms, the idea was that the lower salaries for young players would inflate veterans’ contracts. And indeed, those contracts can be huge. But as all the executives who have read Moneyball are seasoned to do, they saw a flaw in the system. Because younger players had to be paid less, they became unbelievably more valuable. In turn, the lucrative long term deals that players toiled years to earn started to be viewed as radioactive.

That’s part of the reason why it took so long for mega-free agent Manny Machado to find a home this offseason. It’s why Bryce Harper still hasn’t found a home. It’s why the Dodgers shipped away fan-favorite Yasiel Puig, and the Red Sox didn’t bring back stud closer Craig Kimbrell. It’s why Cubs owner Tom Ricketts, when asked why his team hadn’t spent more, responded, “We don’t have any more.”

That’s not true. They have plenty of money; they’re just not willing to use it like they once did. Spending money in the MLB, it seems, has become taboo.

Dodgers president Andrew Friedman values depth when building his teams. In the last four years, the Dodgers have had at least 52 players play for the big league team every season.

What’s the current financial situation in the league? Machado’s deal just surpassed Alex Rodriguez’s as the largest free agent contract in MLB history. When A-Rod’s deal was signed in 2007, the MLB’s revenue was $6 billion. Last year, the league earned $10.3 billion. It’s understandable that contracts today would be more valuable. In addition to the league revenue, teams are bringing in lucrative local TV deals. The Cubs say they’re out of money, but they just announced a new partnership with Sinclair to launch a dedicated cable channel. The exact figures haven’t been disclosed yet, but the Dodgers have a similar partnership with Time Warner for 25-years and $8.35 billion. Still, the Dodgers recently told potential investors that they do not plan to spend above the luxury tax limit for at least four years, according to the Los Angeles Times.

So, what we have now are big market teams that don’t spend the type of money that they used to. Since Andrew Friedman—the subject of Keri’s The Extra 2%—took over the Dodgers, the biggest deals he’s made are a three year, $93-million extension for Clayton Kershaw, the best pitcher of his generation, and a five-year, $80-million extension for superstar closer Kensley Jansen. In the pre-2003 world in which Moneyball was written, those contracts barely even register.


Let’s do an exercise that, I imagine, is not too far from what Billy Beane and Co. did years ago in Oakland. How would you win in this unfair game today? If you’re a small market baseball team, how do you compete? Where are the inefficiencies?

San Diego Padres GM A.J. Preller presented a radical hypothesis yesterday with Machado’s record-breaking deal. The most undervalued players might just be the most expensive.

Consider these numbers. Since 2009 (which is as far back as Forbes keeps track of MLB franchise values) the Yankees value has increased 267%. In that same time period, their payroll has shrunk by 80%. Meanwhile, the Padres have seen a 317% jump in the value of the franchise. After signing Machado, their payroll has increased 245% during the last decade.

The Padres’ progression makes sense. The Yankees doesn’t.

Padres GM AJ Preller might have found the new Moneyball by signing Manny Machado.

But that’s just one way to view value. Here’s another. Machado’s salary is now 6.64 times more than the MLB average, but last year, he was worth 5.7 wins above replacement. In other words, the Padres are paying Machado about six times the average ballplayer, and he’s valued at about the same. And because of the way the league has grown, they can afford the star—and will be able to afford him in future years, thanks to a loaded farm system that guarantees they’ll pay many of their best players pennies for the next six years. The biggest free agent deal in baseball history is the result of a market not valuing superstars correctly. In fact, it’s not valuing them at all. The Padres took advantage of the inefficiency. Billy Beane would be proud.

Yesterday, a reporter asked Cubs general manager Jed Hoyer, who used to work in San Diego, his thoughts on the deal. “In 2010 my payroll was $38.5 million when I was GM of the Padres,” Hoyer said. “That was my thought. Times have changed.”

In truth, San Diego hasn’t changed much. It’s teams like Hoyer’s in Chicago that have. To win a game as imbalanced as baseball, the Padres have to spend like those teams of the past. It’s funny how things come whole circle, isn’t it?

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